Book Holiday Homes in Oakland
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Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Oakland
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
The Three Cornered Pond Retreat | House in Augusta with kayaks & dock access
Charming Wilton Vacation Rental w/ Fire Pit
Veedon Fleece on the Lake
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Lakefront, Stunning Home only 30 min to Sugarloaf!
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Oakland Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oakland vacation homes are the perfect way for you to wing it.
Holiday houses in Oakland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oakland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oakland adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oakland with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oakland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Oakland Holiday Homes essential information
Accommodation | 125 Holiday Homes |
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Lowest Price | NZ$426 |
Highest Price | NZ$426 |
Popular accommodation | Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly, Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME, The Three Cornered Pond Retreat | House in Augusta with kayaks & dock access, Charming Wilton Vacation Rental w/ Fire Pit, Veedon Fleece on the Lake, Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak, Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK, Lakefront, Stunning Home only 30 min to Sugarloaf!, Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away. |
More accommodations in Oakland
Top trending hotels in Oakland
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Central Maine Apartment offering 4 Seasons of Fun.
Cozy Long Pond cottage, private mooring at the community beach. Bring your boat!
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
More ways to explore Oakland
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^Subject to availability and chosen travel dates.